I was in the first 24 months of my first startup, a B2B services business. My team and I had been pursuing a contract at one of the highest-profile early stage companies in the United States, and to our amazement we actually won the deal.

Our revenues tripled overnight, and it put our company on the map.  As excited as we were to win the business, had I known then what I was about to experience I would have managed things very, very differently.

Winning this deal nearly became a death sentence for my business.  Here's why:

Servicing the account consumed all of our resources.

Winning this deal was akin to the dog catching the car: we latched on to the bumper and quickly realized that we had zero control over what would happen next.

I knew that this account would require us to marshal most of our resources - cash, time and people - to deliver on our promises. Quickly we realized just how understaffed we were in order to meet expectations, and pulled nearly everyone into the mix; we more than doubled the company's headcount within 60 days of the program going live.

Our cash funded the headcount growth, our new hires consumed all of our management time, and our inability to do anything but service this customer prevented us from developing the systems and processes that would have made the model replicable.  Our lack of bandwidth also prevented us from winning any new business, which became problematic down the road.

This customer knew they were our biggest account by far, and they took full advantage of that dynamic. Every meeting request, every late night phone call, every weekend email barrage -- we couldn't say no.  

Customer concentration put our balance sheet under immense stress.

I didn't have the bandwidth to service new business, and I didn't have the cash flow to expand the sales team to add more business. In fact, the last thing I wanted at the time was another account to service. This was flawed thinking, as I came to find out soon enough.

Our customer's business was growing exponentially, and our relationship with them grew in lockstep. It was exhilarating, but it was during this time that I learned a priceless lesson about hyper-growth: it's a cash furnace.

Our billings with the customer doubled, we doubled our headcount, and our payroll would also double. The payroll debits hit every two weeks, but our customer's checks came every 60 days.  Before I knew it, I was tapped out on a $1 million line of credit (personally guaranteed, of course) just to float our customer's growing receivables.  They weren't aging more than 60 days, but they were growing so rapidly that my credit line couldn't keep up.  I nearly grew myself out of business.

Losing the business was catastrophic.

I received the call two years into the relationship at the contract renewal: this company was bringing these operations in-house. There was no hint that this result was going to happen. Over forty percent of my revenue evaporated overnight.

We hadn't done the work to diversify the business (we were cash poor, after all) so I had nowhere to put all of these now-idled people. In one of the toughest days of my entrepreneurial career, I had to send 20 amazing individuals packing on little notice.  It was one of those soul-crushing moments that hardens you as an entrepreneur.

About those receivables: the customer's interest in paying us in a timely fashion for services already billed dropped precipitously after the cancellation. I spent the next six months fighting off the bank while I worked to get this now former customer to pay their outstanding invoices. On more than one occasion, I tapped personal savings (including a 401(k) loan) to make payroll. It was a decidedly not-fun experience.

Looking back on this entire episode, the mistakes that I made are glaringly obvious. Seeing only massive revenue gains, I failed to anticipate the negative impact on our operations.  We didn't add new customers, because we didn't have the cash flow or bandwidth. I was naive about setting a customer credit policy.

Sometimes, landing the whale can be the worst thing possible for your business.  In this case, the worst thing for my last company became the best hard-knock education as an entrepreneur that I've ever received.

Published on: Apr 12, 2018